Water → HCID 178487677, compound

HRID 1803698Notes

Reaction equation

HRID 1803698 reaction equation
[C:1]([C:4]1[C:9]([NH:10][C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH:19]([CH3:21])[CH3:20])[N:14]=2)=O)=[C:8]([CH3:22])[C:7]([O:23][CH3:24])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[OH-].[K+].O>N1C=CC=CC=1>[OH:3][C:1]1[C:4]2[C:9](=[C:8]([CH3:22])[C:7]([O:23][CH3:24])=[CH:6][CH:5]=2)[N:10]=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH:19]([CH3:21])[CH3:20])[N:14]=2)[CH:2]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 579564066-Isopropylpyridine-2-carboxylic acid (6-acetyl-3-methoxy-2-methyl-phenyl)amide

Product 1

HCID 178487677HCID 178487677, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
133 °C

Procedure

To a solution of 6-isopropylpyridine-2-carboxylic acid (6-acetyl-3-methoxy-2-methyl-phenyl)amide (107, 0.70 g, 2.14 mmol) in pyridine (5 mL) were added 2.5 equivalents of freshly grounded KOH along with water (50 μL). The mixture was heated by microwave irradiation at 133° C. for 55 min, then 80-85% of the pyridine was evaporated under reduced pressure. The residue was poured on ice and neutralized with acetic acid. The precipitate was filtered off, then dried to give 0.62 g (95%) of the title compound 108 (1.8 g, 95%): m/z=309 (M+H)+.

Workup

  1. custom80-85% of the pyridine was evaporated under reduced pressure
  2. additionThe residue was poured on ice and neutralized with acetic acid
  3. filtrationThe precipitate was filtered off
  4. customdried

Sources & evidence

ORD record
ord-eba78dc41a8d4e2ab0195b4551a020c7
Source dataset
uspto-grants-2013_01
Patent number
US08349869B2

Reaction notes

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